My Suitcase for a Week-Long Trip to the Caribbean

When it comes to clothes, I often overpack. Anyone else, too?

How many shirts do I need? What if I ruin my pants? Is an extra 5 pairs of underwear enough? Will I need this jacket?

Let’s get down to it.

Packing is hard. Especially when you’re excited. (and when your cat really really wants to come too)

The hardest terms to come to: Only pack clothes that you ACTUALLY WEAR.

Sounds silly, right? Well, if you’ve never worn that cute dress before but you think you might this time – just think about it.

Why haven’t you worn it? Does it fit right? Oh right, I forgot it sags weirdly in my armpits. Or maybe you actually do love it, you just haven’t found an occasion to wear it yet. That’s fine, then throw it in the suitcase!

When these new items start to add up though, sometimes it can get to be too much. We hate to admit it, but in the moment, we often go for the clothing that we’re familiar and comfortable with. It’s just human nature.

We often have too high of hopes for ourselves… “well, maybe I’ll actually wear it this time. Yeah. Maybe.” Sound familiar? Then you end up only wearing a big t-shirt over your bathing suit everyday and you don’t even touch those cute, bold tops all weekend.

Bring a statement item or two, something new to show off, but limit those types of choices. Your suitcase is already full enough!

Shoes… How many? Which ones?


What do you actually wear? What do you KNOW won’t give you blisters? What is cute but versatile?

If you’re looking to dress up while on vacation (I’m talkin’ a fancy dinner or two), then bring a pair of sandals or something that you can also wear with a casual outfit.

Don’t forget those cheap flip flops that won’t take up nearly any room in your suitcase. You may want to wear those to the beach instead of your new Birks or other nice sandals.

You’ll want to wear the “favorite shoe” on the plane ride (that one you throw on because it’s comfy, easy and matches mostly anything). The key here is that you’ll be comfortable walking around an airport in these – for me, Nike Air Force sneakers.

The whole shoe category really depends on what you’re planning to do while on vacation – shopping, fancy dinners and photo shoots, or swimming, hiking and boat rides (or maybe a bit of both). Try to stick to maybe 3 pairs – comfortable, cute and easy.

Alright, just get to the list already…

Vacation Time: 8 days, 7 nights

Here’s a little peak into my suitcase!

The Outfits:
  • 5 nice dinner outfits
  • a t-shirt a day
  • a few cute but casual outfits in mind
  • that statement outfit that you KNOW you want a picture in šŸ˜‰
The Items:
  • 2 pairs of jean shorts
  • 2 cute shorts: black flowy, brown “waffle” texture
  • 1 pairs of jeans
  • 1 pair of sport leggings
  • 2 pairs of sleep shorts
  • 1 pair athletic shorts
  • 8 basic t-shirts
  • 2 cute & cropped t-shirts
  • 2 neutral tank tops: white, tan
  • 1 dressy top
  • 1 cardigan/light jacket
  • 3 fancy-ish
  • 2 casual but can be dressed up
  • 1 bar/nightclub dress
  • white Nike Air Force sneakers
  • dressy sandals: neutral & black
  • basic brown Birkenstocks
  • cheap flip flops
  • 3-5 bathing suit pairs
  • 1 cover up (or just use those t-shirts)
  • travel-size shampoo & conditioner (optional: there’s usually hotel shampoo)
  • skincare products
  • toothbrush & toothpaste
  • any medications
  • electronics: phone charger, camera, watch
  • 2 necklaces
  • underwear + socks (with a few extra)
  • wallet
  • purse
  • sunglasses
  • small-sized sunscreen
  • backpack (carry on)
  • tote bag (foldable, easy, good for the beach)
  • jacket for when you come back to cold weather

That’s about it!

Don’t overthink the whole packing situation. Bring clothes you’re comfortable with and love, maybe throw in some new outfits to show off, and make sure you have comfy shoes. That’s all that really matters šŸ™‚

Oh, and don’t forget your sunglasses. Someone always manages to forget those, I swear. (Unless airport shades are your thing… no judgement here)

Yours Truly,

Cat Taylor

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